| Dumbarton v Forfar Athletic FC 25/04/1966 | View match | |
| Albion Rovers FC v Dumbarton 27/04/1966 | View match | |
| Dumbarton v Cowdenbeath FC 30/04/1966 | View match | |
| Airdrieonians (Old) v Dumbarton 13/08/1966 | View match | |
| Dumbarton v Queens Park FC 17/08/1966 | View match | |
| Dumbarton v Queen Of The South FC 20/08/1966 | View match | |
| Forfar Athletic FC v Dumbarton 24/08/1966 | View match | |
| Dumbarton v Airdrieonians (Old) 27/08/1966 | View match | |
| Queens Park FC v Dumbarton 31/08/1966 | View match | |
| Queen Of The South FC v Dumbarton 03/09/1966 | View match | |
| Dumbarton v Raith Rovers FC 07/09/1966 | View match | |
| Clydebank FC (Old) v Dumbarton 10/09/1966 | View match |